ChemicalBook CAS DataBase List (1R,3aR,7aR)-1-((2R,5S,E)-6-hydroxy-5,6-diMethylhept-3-en-2-yl)-7a-Methylhexahydro-1H-inden-4(2H)-one

(1R,3aR,7aR)-1-((2R,5S,E)-6-hydroxy-5,6-diMethylhept-3-en-2-yl)-7a-Methylhexahydro-1H-inden-4(2H)-one synthesis

9synthesis methods

Product Name:(1R,3aR,7aR)-1-((2R,5S,E)-6-hydroxy-5,6-diMethylhept-3-en-2-yl)-7a-Methylhexahydro-1H-inden-4(2H)-one
CAS Number:95716-68-0
Molecular formula:C19H32O2
Molecular Weight:292.46

21343-40-8
158 suppliers
$64.00/500μg

(1R,3aR,7aR)-1-((2R,5S,E)-6-hydroxy-5,6-diMethylhept-3-en-2-yl)-7a-Methylhexahydro-1H-inden-4(2H)-one

95716-68-0
52 suppliers
inquiry

Yield:95716-68-0 32.8%

Reaction Conditions:

with potassium permanganate in water;ethyl acetate at 20; for 4 h;Product distribution / selectivity;

Steps:

13

A solution comprised of potassium permanganate (1.58 g, 0.01 mol) dissolved in purified water (100 mL) was added at room temperature to cerite (5 g) that had been washed with hydrochloric acid. The mixture was intimately stirred for 30 minutes after which the water was removed under reduced pressure, yielding supported potassium permanganate as a dark purple solid (6.60 g, about 1.5 mmol/g). A 340 mg (0.51 mmol) quantity of this solid was weighed out and added to water-saturated ethyl acetate (0.2 mL). A solution comprised of 25-hydroxyvitamin D₂ (20 mg, 0.048 mmol) dissolved in water-saturated ethyl acetate (0.2 mL) was added dropwise at room temperature. The mixture was reacted for 4 hours at room temperature and the solid was removed by filtration. The filtrate was concentrated, and separated and purified by preparative TLC (Hex./EtOAc = 2/1), yielding the targeted product in the form of white crystals (4.6 mg, 32.8 %). By the same method as above, the following reaction was implemented using silica gel (acid), alumina (acid), alumina (basic), or montmorillonite K 10 instead of cerite washed with hydrochloric acid. The results are given below together with those for the reactions employing cerite washed with hydrochloric acid (washed cerite). [Show Image] Reagent Solvent Yield (%) 1KMnO₄/silica gel (acid)EtOAc (sat. H₂O) 22 2KMnO₄/alumina (acid)EtOAc (sat. H₂O) 29 3KMnO₄/alumina (basic)EtOAc (sat. H₂O) 31 4KMnO₄/washed ceriteEtOAc (sat. H₂O) 33 5KMnO₄/montmorillonite K10CH2C12 (sat. H₂O) 27